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Cindy-Ann Boisson | Comedy, Honesty & Owning the Trini Accent

This week on The Corie Sheppard Podcast, comedian Cindy-Ann Boisson joins me for a hilarious and powerful conversation about the craft of stand-up, surviving the grind, and staying authentic. We talk about her upcoming comedy competition Punched Up, why repeating jokes is part of the art form, and the balance between silence and punchlines.

Cindy-Ann shares raw stories—from almost being assaulted in Florida and escaping by diving out of a moving car, to navigating U.S. comedy clubs with her unapologetic Trini accent. We get into what makes Caribbean audiences unique, why she insists on “no intermission” shows, and her Red Woman Tour that’s taking Caribbean stand-up to stages across North America.

This episode blends sharp humour with deep honesty about tragedy, time, gender bias in comedy, and the challenge of creating space for Caribbean women on international stages.

Click the link in my bio for the full episode.

#coriesheppardpodcast #cindyannboisson #standupcomedy #trinicomedy #culture

0:00 Welcome and Introduction to Cindy-Ann

15:25 Punched Up: Creating a Stand-Up Comedy Competition

30:12 The Art of Working Out Jokes and Stage Presence

45:20 Embracing Cultural Identity in Comedy

1:02:35 From Tragedy to Comedy: Personal Storytelling

1:19:18 Comedy Career Beginnings and Development

1:30:56 Gender Barriers in Comedy

1:38:27 Comedy Inspirations and Mount Rushmore